Pinacol → HCID 57822466, compound

HRID 1615913Notes

Reaction equation

HRID 1615913 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12]/[CH:13]=[CH:14]/[B:15]([OH:17])[OH:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[C:19]([C:22](O)([CH3:24])[CH3:23])([CH3:21])[CH3:20].S([O-])([O-])(=O)=O.[Mg+2]>CCOCC>[CH3:20][C:19]1([CH3:21])[C:22]([CH3:24])([CH3:23])[O:16][B:15](/[CH:14]=[CH:13]/[CH2:12][NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[O:17]1

Participants

5

Reactant 3

HCID 6425PinacolHCID 24083Sulfuric acid magnesium salt (1:1)HCID 57822475HCID 57822475, compound

Product 1

HCID 57822466HCID 57822466, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (E)-(3-(((benzyloxy)carbonyl)amino)prop-1-en-1-yl)boronic acid (2.38 g, 10.14 mmol), pinacol (1.418 g, 12 mmol), and magnesium sulfate (2 g, 16.62 mmol) in ether (25 mL) was stirred for 2 days. The mixture was filtered and concentrated. The crude material was purified by silica gel chromatography using 0-30% EtOAc/hexane as the eluent to give (E)-benzyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)allyl)carbamate as a clear oil (1.6 g, 50%). LCMS: Rt=3.66 min, 77%, (M+H)+=318, (M−H)−=316.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. customThe crude material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-343b1069703c4af0b4d0aa217071312f
Source dataset
uspto-grants-2014_07
Patent number
US08765767B2

Reaction notes

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